tert-Butanol → tert-Butyl (3-isobutylcyclobutyl)carbamate
Reaction equation
[CH2:1]([CH:5]1[CH2:8][CH:7](C(O)=O)[CH2:6]1)[CH:2]([CH3:4])[CH3:3].[C:12]([OH:16])([CH3:15])([CH3:14])[CH3:13].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.C([N:36]([CH2:39]C)CC)C>>[CH2:1]([CH:5]1[CH2:6][CH:7]([NH:36][C:39](=[O:24])[O:16][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:8]1)[CH:2]([CH3:3])[CH3:4]Participants
5
Conditions
- Temperature
- 95 °C
Procedure
3-Isobutylcyclobutanecarboxylic acid (3.00 g) and tert-butanol (30 mL) were mixed. To the mixture were added triethylamine (4.28 mL) and diphenylphosphoryl azide (5.38 mL) at ice temperature. After stirring at 95° C. overnight, the reaction mixture was concentrated in vacuo. To the resultant residue was added ethyl acetate. The mixture was washed with water and brine, then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/40) to give the title compound (2.91 g).
Workup
- concentrationthe reaction mixture was concentrated in vacuo
- additionTo the resultant residue was added ethyl acetate
- washThe mixture was washed with water and brine
- dry with materialdried over magnesium sulfate
- filtrationThe magnesium sulfate was filtered off
- concentrationthe filtrate was concentrated in vacuo
- customThe resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/40)
Sources & evidence
- ORD record
- ord-38a14eaa31c44156ae991e30b708c2db
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08604069B2
Reaction notes
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